Midlife Regrets Are Inevitable. Here's How to Make Them Work For You
Reading time: Approx. 5 minutes
Ever catch yourself at 3 am, thinking about that business you never started or that job move you didn’t pursue? Or the friendship you let fade away? The creative passion you abandoned for a "sensible" career?
I know that I have. If you have too, you're not alone.
As we move through our 40s and 50s, we reflect more deliberately on the paths we've taken - and especially those we haven't. This reflection often leads to a growing desire to realign our lives.
At this time of year, these thoughts are even more prevalent. Christmas and New Year are wonderful celebrations; a time for joy and togetherness with those we love. But they also tend to evoke a deeper reflection on the state of our lives – and the dreams, hopes, and aspirations we have for the future.
In doing so, many encounter a familiar companion: regret.
Yet, in a culture that celebrates "no regrets" as a badge of honor, we rarely talk about these uncomfortable companions. We’ve learned to say we have “no regrets,” even when we have, but carry them quietly.
But regret shouldn’t be shameful. It’s not failure. It’s human.
And the good news is that understanding how to use it constructively can be a valuable guide for decision-making, especially as we navigate our second half.
Why regret hits differently in midlife
Midlife brings a growing awareness of time's finite nature. That feeling of endless possibilities you had at 25 shrinks. Suddenly you're tallying up your choices – both the ones you made and the ones you didn't.
This isn't just philosophical musing - it's neuroscience. Our brains process regret differently as we age, with a sharper focus on opportunities missed rather than mistakes made. Research shows that over time, we regret inactions (things left undone) much more than actions (even failed ones).
When we act, and things go sideways, we can usually find meaning: "At least I learned something" or "It led me somewhere unexpected but good." But with chances never taken, our minds can torture us with endless possibilities; all the great things that could have happened but didn’t.
This is why that abandoned career transition, the relationship you didn’t nurture, or the risk you played too safe can suddenly feel so pressing at 45 or 55. The timeline has shifted – the opportunity space seems narrower while the accumulated potential for regret is wider.
I’ve had my share of regrets. Career moves I didn’t make (like that CEO role I was en route to get), places I didn’t get to live in (such as the Big Apple, of course), real estate investments I didn’t make (it took me way too long to get back on the market after we returned to Denmark), and friendships I didn’t hold on to.
From one perspective, this is simply life. Things happen, or they don’t, and we try to push them out of our minds to avoid the pain they might bring. From another perspective, they are opportunities to learn so I can make better choices in the future. More on that later; first, let’s understand regret a little better. They aren’t all equal.
Four common types of regrets
Based on extensive research by Daniel Pink and others, four types of regret consistently surface across cultures:
Foundation Regrets – "If only I'd made the effort." These stem from failing to build stable foundations in health, education, or finances. The executive who sacrificed health for advancement or the entrepreneur who neglected retirement planning. These regrets often surface when we realize the compound effect of early choices.
Boldness Regrets – "If only I'd taken the chance." These arise from playing it safe rather than pursuing dreams, speaking up, or taking risks. The passion project you never launched. The move abroad you talked yourself out of. The person you never asked out. The promotion you didn't actively pursue.
Moral Regrets – "If only I'd done the right thing." These emerge when we've compromised values or treated others poorly. The colleague you undermined. The white lie that grew. The time you kept silent when you should have spoken up. These stick - and may even increase in midlife, along with growing moral awareness - because they cut to the heart of who we are and aspire to be.
Connection Regrets – "If only I'd reached out or invested more." These reflect relationships we've let drift or never repaired, from friendships to family bonds. The parent you never reconciled with. The friend who drifted away during your career climb. The children who grew up while you were sprinting on the hamster wheel.
For those in their 40s-60s today, boldness regrets often sting most. Many of us have followed scripts of stability, loyalty, and security in our careers and lives, only to question whether we've been true to ourselves. Now we wonder what adventures we missed by playing it safe.
Making peace with past regrets
We’ll start with something I find interesting and somewhat counterintuitive: Reversible decisions actually cause more regret than irreversible ones.
You would think that reversible decisions should feel safer because you can always change your mind. And that irreversible decisions should feel scarier because the stakes are high. But the opposite is often the case.
When a choice feels reversible, our minds stay open, constantly comparing alternatives and wondering “what if?” Irreversible decisions, on the other hand, create clarity and commitment. The mind shifts from evaluation to adaptation.
Once something cannot be undone, the brain works harder to make peace with it, regardless of the outcome.
But what about all those choices that were reversible at the time they were made?
Before we can move forward with peace in mind, we need to process what's behind us. It requires us to think of regret as something we do rather than something we have. It’s a feeling, of course, but it’s as much a process.
Here are some ways to approach it:
Accept the inevitable. Every life contains regret because every choice closes doors. In a sense, it's simple math. Feeling regret means you lived a life rich with possibilities and strived for more. The alternative - a life so narrow that regret never appears - would be far worse.
Extract the wisdom. Ask yourself: "What does this regret reveal about what matters most to me?" Regret is a window into your core values. The career path not taken shows what kind of work energizes you. The relationship regret reveals what connections you truly value. Think of it as intelligence gathering for your next chapter.
Practice self-compassion. You made past decisions with different information, maturity, and circumstances than you have now. As one friend told me: "I couldn't possibly have known then what I know now, so why do I keep judging myself as if I should have?" We often downplay the context of past choices. Forgive your earlier self so you can focus on the future.
Repair what you can. If an existing regret is actionable, act – it’s one of the best antidotes to regret. Many regrets are partially within our control to mend. The act of attempting to fix things can reduce regret. Even if you can't fix it and erase the regret, you'll likely feel relief that you did what was in your power.
Talk about it. There's growing evidence that articulating regrets - whether through conversation or writing - reduces their emotional charge. Sharing your regrets and the lessons you've learned can transform pain into wisdom and help others, too.
Enabling a lower-regret future
A couple of years ago, when I first dove into the topic of regret, I was curious about what I could practically do today to minimize the risk of future regret. I’ve distilled the main findings into five points that together form a sort of guidance system for me.
Some are easier to practice than others, but I think there’s value in all if you lean in:
Run the "future regret test." When facing decisions, project yourself 20 years into the future and ask: "How would I feel about not having made this choice?" This mental time travel cuts through immediate fears and connects you to deeper values and priorities.
Default to action. Remember that inaction creates more lasting regret than (thoughtful) action. This doesn't mean recklessness - it means recognizing when fear of discomfort is the only thing holding you back. Ask yourself: "Am I avoiding this because it's truly wrong for me, or because it's uncomfortably right?"
Set “no-regret” boundaries: Protect what matters by creating boundaries around key priorities. If family time is essential, block off work-free hours. If creative expression or healthy practices matter, schedule time for them. Treat these boundaries as investments in your future self.
Broaden your identity. Today's uncertain world rewards those who build diverse sources of meaning, income, skills, and connection rather than gambling everything on a “narrow identity”. This creates both resilience and multiple avenues for fulfillment. The most satisfied midlifers I know have developed what some call "identity diversification" - drawing meaning from a variety of roles and pursuits.
Make decisions (feel) irreversible. Practice creating closure. When you’ve made a choice, then deliberately commit to it, fully. Remove unnecessary escape routes and alternatives. Stop second-guessing yourself.
They’re working for me. Not perfectly, but they’ve made me more aware and focused whenever I face a high-stakes decision.
Regret remains a paradox, though: acknowledging it seems to be the way to avoid being consumed by it. Rather than seeing it as an enemy, embrace it as a teacher.
